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tert-Butyl methyl ether → HCID 11151078, Verbindung

HRID 541062
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 541062
[CH:1]([CH:3]1[C:15]2[CH:14]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:2].[BH4-].[Na+].C(NC1C=CC2C3C(=CC=CC=3)CC=2C=1)(OC(C)(C)C)=O.CC(OC)(C)C>CO.O.CCOC(C)=O.CC(O)=O>[OH:2][CH2:1][CH:3]1[C:15]2[CH:14]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 15413tert-Butyl methyl etherHCID 4311764Sodium borohydrideHCID 113120632-(Boc-amino)fluoreneHCID 11347396HCID 11347396, Verbindung

Produkt 1

HCID 11151078HCID 11151078, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176
Acetic Acid
Lösungsmittel
HCID 887MethanolLösungsmittel
HCID 962WaterLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

9-Formyl-2-(Boc-amino)fluorene was suspended in 100 ml methanol and 2.0 g NaBH4 [52.9 mmol, 1.1 equiv with respect to the starting 2-(Boc-amino)fluorene] was added portion wise. The suspension that rapidly cleared up was magnetically stirred until the starting product disappeared for 4 h at room temperature [TLC, Rf=0.57, PE:MTBE (1:2)]. The reaction mixture was diluted with 300 ml H2O and acidified with 15 ml glacial HOAc to pH 5.0, and the precipitate was directly dissolved in 150 ml EtOAc. The organic phase was washed with 3×50 ml sat. NaHCO3 and 1×50 ml brine and dried over anhydrous Na2SO4. The solvent was rotary evaporated to give a solid, which could be used without further purification. The product was analyzed by NMR (13.1 g, 88% yield).

Aufarbeitung

  1. washThe organic phase was washed with 3×50 ml sat. NaHCO3 and 1×50 ml brine
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe solvent was rotary evaporated
  4. customto give a solid, which
  5. customcould be used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-8693e7a9f034413699b32c934df96c9f
Quelldatensatz
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08871949B2

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